Phenol → HCID 10181102, compound

HRID 1070872Notes

Reaction equation

HRID 1070872 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16](Cl)[N:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:14]=2[CH:26]=1.C(=O)([O-])[O-].[K+].[K+].[C:34]1([OH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([N:15]2[C:14]3[CH:26]=[C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:2])=[O:27])[CH:11]=[CH:12][C:13]=3[N:17]=[C:16]2[O:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 69435062HCID 69435062, compound

Product 1

HCID 10181102HCID 10181102, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

150 mg of 6-[[2-chloro-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was dissolved in 2 ml of dimethylformamide, mixed with 54 mg of potassium carbonate and 37 mg of phenol, and the mixture was stirred for 7 days at 150° C. After cooling, it was mixed with saturated ammonium chloride solution, diluted with water, extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 78 mg was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with ethyl acetate
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was purified by column chromatography on silica gel
  7. custom78 mg was obtained

Sources & evidence

ORD record
ord-25215682fab3481194ef8179315b2c90
Source dataset
uspto-grants-2005_06
Patent number
US06903126B2

Reaction notes

Loading…